I used MacENC years ago, and was in contact with the dev at that time to fix some things in the early vector implementation. He was great to work with, and I personally like the program a lot. Also I have used OCPN which has become very full-featured and has the advantage of displaying the old worldwide Cmap charts floating around the internet
(great as fallback). I have only briefly tried Polar Navy
but did like what I saw. You can't lose with any of these.
WINE does work for most Windows applications, depending on what APIs they call. I avoid like the plague Windows programs but do keep a Windows instance as a virtual machine (without network access) to run those few Windows-only apps. Boot Camp is more efficient so if you wanted Windows for games then the extra speed would be worth rebooting into Windows. Otherwise the virtual machine approach is more convenient. But best to use Mac applications as they almost always have better GUI design, if not every possible (unnecessary) feature.